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Holiday Villas with Pool in Italy

Below you will find our entire range of Italian holiday villas with pool. To narrow down the list, you can select the number of persons, and additional amenities (private pool, child safe pool, heated pool, near the beach, etc.). Don’t forget to click the search button.

Maramai
Tenuta di Gracciano

Maramai

Comfortable villa with great pool on wine estate near Montepulciano and Pienza

Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer’s family who lived there until the e...

Key activities:

visiting the wine estate, cultural sightseeing, excellent food, hiking, tennis (village)

As from 2370.00 €

9 5 5 Pool Internet Access Florence: 120 km
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Pera 1
Borgo di Pietrafitta

Pera 1

Ground floor apartment on the edge of the hamlet

The Casa Pera is an ancient building within the hamlet, formerly used as lodging and warehouse. It has been cleverly converted into 4 separate units and decorated b...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 805.00 €

3 2 1 Pool Internet Access Florence 47km
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La Capanna
Borgo di Pietrafitta

La Capanna

Converted shed in the heart of the Chianti

This used to be a simple shed on the edge of the hamlet. It has been turned into a dream haven for two or three people.
A large living room with open plan kitchen,...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1225.00 €

3 2 1 Pool Internet Access Florence 47km
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Granaio 1
Borgo di Pietrafitta

Granaio 1

A converted granary

What used to be the granary of the estate has been cleverly converted into two ground floor apartments, each with its own private garden space.

This apartment ha...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1146.00 €

4 2 1 Pool Internet Access Florence 47km
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Villa Strozzi
Collegalli

Villa Strozzi

Entire wing of an Tuscan villa with out of this world views and pool

Situated on the grounds of the Collegalli Estate in Montaione, the origins of Villa Strozzi date back to the 12th century. With its 19th century interior...

Key activities:

pool dipping, sun bathing, wine sipping, culture, local markets, glorious countryside and day trekking

As from €

14 7 5 Pool Internet Access Pisa 60 km (1h)
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Casa Livia
Cetona

Casa Livia

Medieval tower with pool, views and in walking distance of a village

Savor the best of southern Tuscany at this wonderful three-bedroom 14th century tower is set within bucolic gardens clinging to the hillside at the edge of the pict...

Key activities:

touring towns, cultural sightseeing, visiting wine producers, spa treatments, hiking, biking, golf, watersports

As from 1315.00 €

6 6 3 Pool Internet Access Perugia 68km, Florence 140km, Rome 190km
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Bencontenta
Frassanelle

Bencontenta

Luxury villa with private pool on historical estate in northern Italy

Bencontenta is a traditional Venetian farmhouse on the estate of Frassanelle, situated on the...

Key activities:

Sightseeing, golf, hiking whithin the estate, excellent restaurants

As from 2980.00 €

14 7 7 Pool Internet Access Venice: 68 km
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Sassaia
La Foce

Sassaia

Spacious country villa with pool in the famous Val d'Orcia

Sassaia sits on the slopes of the famous Orcia valley and is surrounded by magnificent evergreen oak trees typical of Tuscany. Beyond are open fields and views acro...

Key activities:

cultural sightseeing, winemaking area, tennis, spas, hiking

As from 4750.00 €

14 7 6 Pool Internet Access Florence: 150 km
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Villa Melissa
Fighine

Villa Melissa

19th century luxury villa with pool in Tuscan hamlet between Florence and Rome

Villa Melissa is a large villa set within its own private garden. The beautiful swimming pool with pool house and full changing and shower facilities lies 2 minute ...

Key activities:

cultural sightseeing, visiting wine producers, excellent restaurants, spa treatments, hiking, mountain biking

As from 5809.00 €

8 4 4 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
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Dario 2
Borgo di Pietrafitta

Dario 2

Spacious ground floor apartment with private terrace

This farm used to house the sharecroppers who lived on the estate to tend the land and the animals. 5 families used to live here originally, 5 apartments are availa...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1313.00 €

4 4 3 Pool Internet Access Florence 47km
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